Vitals

Billy Crystal as Harry Burns, recent college graduate

Chicago to New York City, Spring 1977

Film: When Harry Met Sally…
Release Date: July 14, 1989
Director: Rob Reiner
Costume Designer: Gloria Gresham

WARNING! Spoilers ahead!

Background

I graduated from college fifteen years ago this week, and I’m still (slightly) younger than 40-year-old Billy Crystal was when he played recent University of Chicago graduate Harry Burns in the opening scenes of When Harry Met Sally. Directed by the late Rob Reiner (a qualifier which still hurts to say), When Harry Met Sally is considered by many—including yours truly—to be one of the best romantic comedies of all time.

Ironically scored to Louis Armstrong crooning “Our Love is Here to Stay”, the movie begins with Harry kissing a girlfriend whose name he wouldn’t even remember five years later. Amanda (Michelle Nicastro) introduces Harry to her friend Sally Albright (Meg Ryan), who has agreed to drive the stranger across the country to New York, which Sally has calculated should be “an 18-hour trip with six shifts of three hours each.”

The 800-mile drive in her yellow Toyota wagon establishes their dynamic and respective neuroses as they debate dark sides and death, Casablanca and carnal relations, and whether men and women can ever truly be just friends—with Harry denies with all the worldly confidence of an unworldly 22-year-old:

Harry: No man can be friends with a woman that he finds attractive. He always wants to have sex with her.
Sally: So, you’re saying that a man can be friends with a woman he finds unattractive?
Harry: No, you pretty much want to nail them too.

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What’d He Wear?

Unlike some movies or TV shows that take some sartorial liberties in depicting characters falling prey to excessive fashion trends in flashbacks (I’m thinking Miami Vice Chandler and Ross on Friends), When Harry Met Sally‘s costume designer Gloria Gresham keeps Harry Burns’ college style true to his mil-surp/streetwear-informed wardrobe through the rest of the movie. His sporty and unfussy casual attire restrains it to the realm of timelessness more than if he had showed up dressed for the road in an uncharacteristic painted rayon disco shirt open to mid-chest and tucked into bright bell-bottoms.

Instead, Harry wears a plain zip-up hoodie, baseball tee, and jeans—a simple outfit, even for Harry, which feels true for the late ’70s and every following decade as well. Indeed, if you flew back in time to the late 2000s, it’s very likely you’d have seen me dressed almost identically on Pitt’s campus.

Harry’s sweatshirt is made from a heathered gray fabric, likely a soft cotton/polyester blend with a white piled terry lining. It has a straight gray-finished front zip and a gray drawstring hanging down from both sides of the hood, self-tied on each end to prevent the eyelets from eating the cord. The hoodie also has the typical split kangaroo-style front patch pockets flanking the bottom of the zip-up front. The set-in sleeves are finished with narrowly ribbed cuffs that Harry pushes up his forearms.

The hoodie is always seen partially zipped over a T-shirt fashioned with a plain white body contrasted with an indigo crew-neck ringer that extends down onto the raglan sleeves, which are likely ¾-length like most traditional baseball tees.

One of the outfit’s few concessions to the ’70s is still relatively subtle. His blue jeans are clearly Levi’s, though marked with an orange tab sewn along the back-right patch pocket rather than the 501’s classic red tab. Through this period, Levi’s used an orange tab to differentiate their more irregular denim such as these boot-cut jeans with their slightly flared bottoms. The jeans otherwise follow an orthodox design with their five-pocket layout complete with the usual Levi’s arcuate stitch across both back pockets. Harry holds them up with a brown leather belt.

A consistent through-line from Harry’s style in 1977 to the “present day” sequences in the late ’80s are his fondness for tennis shoes. He leaves college wearing a pair of white sneakers with red trim, never seen clearly enough on screen to clearly identify as Nikes like he wears in later scenes.

Harry later adopts more subdued gold wristwatches, but the gold chronograph he straps to a hefty dark-brown leather bund cuff-strap in this sequence is perfectly within character for a brash young student in the 1970s. Originally developed for German Bundeswehr military pilots, bund straps resurged among race car drivers in the 1960s and reached their fashionable peak the following decade among men channeling a daredevil image—even if the closest they get to motorsports is sharing a ride with a young blonde in a 75-horsepower station wagon.

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How to Get the Look

Harry’s ’70s road trip look skips the caricature of retro disco peacocking in favor of the kind of casual clothes too laidback to ever go out of style—a heather-gray zip-up hoodie, baseball tee, Levi’s, and worn-in white sneakers—finished with the subtle swagger of a bund-strapped chronograph.

• Gray heathered poly/cotton zip-up hoodie with kangaroo-style front patch pockets
• White cotton baseball T-shirt with indigo crew-neck ringer and ¾-length raglan sleeves
• Blue denim Levi’s “orange tab” boot-cut jeans with belt loops and five-pocket layout
• Brown leather belt
• White sneakers with red trim
• Gold chronograph on dark-brown leather bund strap

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Do Yourself a Favor and…

Check out the movie.

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The Quote

When I buy a new book, I always read the last page first. That way, in case I die before I finish, I know how it ends. That, my friend, is a dark side.